Potassium Carbonate → HCID 68671567, compound

HRID 2071168Notes

Reaction equation

HRID 2071168 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([N:12]([CH3:14])[CH3:13])[N:9]=[C:8]([C:15]#[N:16])[CH:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:13][N:12]([CH3:14])[C:10]1[N:9]=[C:8]([C:15]#[N:16])[CH:7]=[C:6]([CH2:5][OH:4])[CH:11]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68672414HCID 68672414, compound

Product 1

HCID 68671567HCID 68671567, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 364 mg (1.66 mmol) of (2-cyano-6-(dimethylamino)pyridin-4-yl)methyl acetate in 7 mL of MeOH was added 365 mg (2.64 mmol) of K2CO3. After 1 h, the mixture was filtered through Celite with MeOH and EtOAc. More EtOAc and H2O (30 mL) were added; the aqueous layer was extracted with EtOAc (4×). The combined extracts were washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (50% EtOAc/hexanes) provided 253 mg of 6-(dimethylamino)-4-(hydroxymethyl)picolinonitrile as a pale yellow solid in 86% yield.

Workup

  1. filtrationthe mixture was filtered through Celite with MeOH and EtOAc
  2. additionMore EtOAc and H2O (30 mL) were added
  3. extractionthe aqueous layer was extracted with EtOAc (4×)
  4. washThe combined extracts were washed with brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-65a59a26feaa460cb2c38e005ad05277
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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